Holiday rentals in Springs

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 482 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Superhost

4.83 out of 5 average rating, 36 reviews

Heated Pool, Hot Tub w/ Fire pit and Kids Games

Walk or bike to Maidstone Beach, Gerard Drive, marinas, and top dining. Peaceful tree-lined street perfect for your Hamptons escape.🌸✨ 🏊‍♀️ Heated pool *(closed until spring 2026) 👙 Hot tub for year-round soaking 🚿 Outdoor shower 🍴 BBQ for easy meals 💃 Close to nightlife 🔥 Fire pit for relaxing evenings 🏡 Private patio 🃏 Indoor games 👙 Lawn games 🚗 Convenient parking ☕ Coffee station "Great house! 5 star review for sure!" -Erica Rental Registration Number HMOT-000157

4.98 out of 5 average rating, 199 reviews

A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.

Flat in The Hamptons

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

4.98 out of 5 average rating, 45 reviews

The sleeping area features a plush bed with white bedding and two neatly arranged pillows. Warm light from the wall-mounted lamps illuminates the space, while green foliage is visible through the large windows on either side, creating a soothing atmosphere.

Flat in The Hamptons

The Hideaway | Clearwater Beach

Your private retreat in the heart of Clearwater Beach, East Hampton! Escape to this serene, design-forward suite nestled in one of the most peaceful corners of the Hamptons. Just minutes from the bay, this luxury hideaway offers the perfect balance of comfort, style and convenience. The space features a plush king bed and all the amenities you need for a relaxing stay. Sip your morning coffee in your private outdoor space before heading off for a swim at Clearwater Beach.

4.94 out of 5 average rating, 380 reviews

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

Home in North Fork

The Sandpiper

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Superhost

A modern black-clad home is visible with large windows reflecting soft light. Lounge chairs line the pool area, accompanied by umbrellas providing shade. A playful inflatable is positioned in the sparkling aqua pool, framed by lush greenery creating a serene outdoor environment.

4.77 out of 5 average rating, 108 reviews

Spacious East Hampton Getaway with Pool

This bright and comfortable 3 bedroom, 2 bath Scandinavian home awaits! Located just a 5 minute drive Sag Harbor and 10 minutes to the heart of East Hampton to enjoy beaches, shopping, restaurants and bars. The light hardwood floors create a crisp feel that you have to witness. The first floor's two guest beds open out to a lovely eat-in kitchen with dining and living rooms featuring a wood-burning fireplace and pool to check every box for year-round fun.

Guest suite in The Hamptons

A cozy sleeping area is highlighted by a spacious bed with light blue bedding, positioned near a working fireplace. A television is placed on a wooden stand across from the bed. Soft lighting from bedside lamps creates a warm ambiance, complemented by a decorative artwork on the wall.

4.9 out of 5 average rating, 381 reviews

Artists Sag Harbor Village Retreat

This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

A bright living room features tall windows that allow ample natural light. A modern sofa and coffee table are arranged on polished wooden floors. A large copper fireplace serves as the focal point, surrounded by minimalistic decor, creating a spacious and inviting atmosphere.

4.89 out of 5 average rating, 133 reviews

Light-filled Sag Harbor village gem

Midcentury style in the heart of Sag Harbor Historic district. Soaring 20-foot floor-to-ceiling windows and skylights throughout offer the ideal indoor-outdoor experience for enjoying all seasons. Featured in Home & Garden, the house is situated on sprawling grounds, one of the largest lots in Sag Harbor. In the winter, enjoy the Scandinavian sauna and lounge in front of the fireplace. Gunite pool open May 25 to Sept 3.

The living area features two comfortable sofas, a wooden coffee table, and a dining table set for four. A window allows natural light to fill the space, while decor accents create a relaxed environment. Air conditioning unit is visible on the wall.

4.97 out of 5 average rating, 356 reviews

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

4.88 out of 5 average rating, 128 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.

4.94 out of 5 average rating, 65 reviews

A cozy living area features a green patterned accent wall and a comfortable sofa. A television is positioned on a white media stand, while a rustic dining table and chairs are present. A bright red fridge adds a pop of color, and a lofted sleeping area is accessed by a blue-painted staircase.

Flat in The Hamptons

Sunny 1 bedroom Guest Suite w/private entrance

Beautiful apartment with a private entrance, bath and kitchen. Walk to nearby beaches & drive to private marina with grills and picnic tables and enjoy the most spectacular sunsets. Embrace the coastal lifestyle and indulge in the ultimate relaxation in this beautiful and sunny appartment.

A wooden deck features comfortable seating with white cushions, positioned around a small table set with tea and pastries. Lush green grass surrounds the area, dotted with tall trees, while a clear view of the harbor can be seen in the background.

4.83 out of 5 average rating, 41 reviews

Historic East Hampton Home - Private Beach Access

Experience breathtaking sunset views over the harbor from our beautiful mid-century modern home. Designed by Kaneji Domoto, a student of Frank Lloyd Wright, the house seamlessly blends with its stunning surroundings, offering abundant natural light and water views from nearly every room.

Popular amenities for Springs holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Springs

A sleek modern farmhouse exterior is displayed, featuring a heated saltwater pool at the forefront. Comfortable seating arrangements surround the pool area, and expansive glass windows illuminate the interior. Lush greenery borders the property, contributing to a serene outdoor environment.

5 out of 5 average rating, 9 reviews

East Hampton sanctuary

A spacious living area is highlighted by a stone fireplace, flanked by large windows that provide ample natural light. Wooden beams run across the ceiling, complementing the neutral-toned furnishings, including a cozy sofa. A dining table is visible in the background, surrounded by greenery.

4.98 out of 5 average rating, 53 reviews

Chic cottage on lush, secluded acre by the beach.

A spacious living room is featured, characterized by whitewashed beams and large windows allowing natural light. A soft, neutral sofa is positioned in front of a gold-accented coffee table. Decorative plants and a subtle area rug add warmth to the space, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 40 reviews

Hamptons Designer Cottage w Pool by Wölffer Estate

A modern living room showcases a spacious sectional sofa accompanied by a round coffee table. Light wood flooring is highlighted by an area rug. A large kitchen island is visible in the background, complemented by pendant lighting. A staircase leads to the upper level.

4.96 out of 5 average rating, 24 reviews

Winter Inquiry - 5 Bed Village Cottage Retreat

5 out of 5 average rating, 20 reviews

The beachfront home features a wrap-around balcony and large windows that provide views of the shore. The exterior is surrounded by a stone wall and sandy beach, with a staircase leading down to the water from the deck.

Home in North Fork

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

Superhost

A spacious outdoor area features a heated gunite pool surrounded by a wooden deck. A modern black house is visible in the background, with large windows and a covered seating area. Lush greenery frames the scene, creating a serene environment.

4.87 out of 5 average rating, 61 reviews

Cedar Hot Tub, Suana, Heated Pool walk to water

A bright living room features large windows that showcase water views. Comfortable white sofas are arranged around a wooden coffee table, while a dining area is visible in the background. A ceiling fan and a wall-mounted TV add to the room's functionality.

4.91 out of 5 average rating, 46 reviews

Wake up to Stunning Views at a Serene Waterfront Haven

A spacious outdoor area features a heated gunite pool surrounded by natural stone tiles. Poolside loungers are positioned on one side, while a shaded table with umbrellas and a grill are visible on the patio. Lush landscaping and flowering plants enhance the serene environment.